When I tell people that I’m a recovering corporate lawyer turned global vagabond, and that I’ve been traveling the world full time for 3 years while working online, it usually elucidates one of a couple reactions.
But another group of people will stand in shock for a minute before asking simply:
How did that happen?
And honestly, it’s a long and convoluted story.
And I’ve finally decided to tell it in this post.
So grab a cup of coffee, buckle up, and let’s dive into it:
Travel Wasn’t (Originally) My Dream
Growing up, I always imagined myself having a traditional career. I wanted to become a politician. Or a journalist. Or a lawyer. Or something relatively “normal.”
I did all the right things for that path.
I went to an Ivy League university for undergrad, and then managed to get into and graduate from the number one law school in the country – Yale Law School.
But growing up in a financially challenged background meant that I had to fund those seven years of private education with scholarships, financial aid, and student loans.
Lot and lots of student loans.
I graduated with something north of $200,000 in student loan debt.
That basically meant that doing something like a college gap year in Europe was never something on my radar. I didn’t even have the money to study abroad as most of my peers did.
Now don’t get me wrong: I definitely wanted to travel.
Growing up in a military family meant I had lived in a bunch of different places as a child (including 3 years in Japan for middle school) and those experiences instilled an appreciation for travel in me at an early age.
But I just didn’t really have the money for it (or so I thought), and I had other priorities like my career.
So I passed the bar, took a job as a corporate litigator, and settled in for what I thought would be an ambitious but predictable career in the law at a major firm in my hometown of Denver, Colorado.
Changing My Purpose
For five years I followed that path. And everything seemed to be going according to plan.
But then the burnout set in.
Spending 70-80 hours a week at a desk for years on end is not a particularly great recipe for long term mental happiness and well-being.
Even though I actually enjoyed my work, even the sweetest drink is intolerable when you’re drinking out of a firehose.
And something else happened along the way:
I realized that I was defining myself by relation to my career, but that my career was just one tiny part of myself – and that I was stifling the many other parts of me that mattered.
So I left my job and went to work on a political campaign (politics has always been a passion of mine).
And when that election was over, I decided to take a career gap year (or what I originally thought would be a year).
I visited 43 countries in that year and had some pretty incredible experiences.
I took a camper-van around Tasmania with a Dutch pilot I met in an elevator.
I went on safari in Kenya.
I saw the pyramids. And the Taj Mahal. And Machu Picchu.
I met so many incredible people and made so many new friends.
And I changed the way I thought about life.
Redefining How I Think About Work
But after just a few months on the road I realized that I was having the time of my life … and that I didn’t want it to stop.
Whether you care about your lifestyle or your career or nothing in the entire world, you have to make money somehow in order to survive.
And continuing a life of travel meant figuring out a way to make an income.
But since like I felt like my former career wasn’t useful in the online economy (something I’ve later learned is definitely not true of ANY career), I basically decided to start at the bottom and work my way up again.
It was incredibly humbling to look into entirely new industries to consider diving into (photography? travel blogging? videography?), but all of the ones I could think of for some reason were careers that involved travel.
Which is weird because I’ve later realized that was a false limitation I self-imposed upon my options.
But that’s where my mind was so I just did what I could think of.
The first thing I did was to start a travel blog after about 5 months on the road.
But you quickly learn that the issue with starting a travel blog is that it takes an annoyingly long amount of time to generate a full time income (a year is probably the fastest you could make it work in my opinion).
Resetting My Life
And so, in some ways defeated, I came home six months later in search of a job back home in Denver, Colorado.
Had I chosen to go back to being a lawyer, I could have made that happen easily.
I thought about it.
For quite a while.
I wrestled with the decision in my head.
There was so much appeal to going back to the law: the confidence of working in a job you know you can do well, the allure of a stable and more than ample salary, and the prestige of working as an attorney in a society that, for the all the “attorney jokes” it cooks up, still wants its children to grow up to be doctors or lawyers.
But then there was also this sense of dread that spending the next 35 years of my life on that path would involve chaining myself to a desk and pouring myself into a career that may or may not pour itself back into me.
There was also the dread that I might not reach 65 years old, and with it those blissful 12 years (the average American lives to be 77) we reserve for the more physically difficult chapter of our lives.
Becoming an Online Entrepreneur
And so I opted instead to take a more entrepreneurial take on life – to focus my time on efforts that would generate an income (albeit a much reduced one compared to a legal salary), but in a way that I could control better and that would allow me to return to the road.
I started a software company along with a couple partners. Though I was able to lean on my legal background for some of that, much of it involved having to learn a huge new set of skills.
I kept the travel blog cruising along through all of this. And here’s another thing about travel blogging:
It’s also a lot more work than it seems, and requires a lot of skillsets.
So that meant I had to teach myself SEO, social media marketing, graphic design, web design, photography, drone photography (who am I kidding, that one was for me!), videography, video editing, and a dozen other skills I’ve probably forgotten that I never had before this.
Those skills came in handy for my software company I co-founded with two partners.
Founding a start-up requires not only working for free, but actually contributing money to the company at the start, which meant eating into my dwindling savings (which I needed to settle my still not paid-off student loans).
Committing Fully to the Digital Nomad Lifestyle
So after a couple months back home in Denver, I decided to take advantage of geo-arbitrage and to get back out on the road. And that’s why I packed up my bags again and headed to Merida, Mexico.
I did a bit of freelance travel writing to help pay the bills, but I spent a lot of time working on my start-up and my travel blog there. Eventually, my travel blog began to finally gain some meaningful readership and produce a small but modest income.
In the meantime, I lived a simple, affordable life in a place where that could be done for less than a $1,000 a month, all in.
A few months later I moved to a nearby but very different base: Playa del Carmen.
Playa is slightly more expensive than Merida, and lacks Merida’s colonial charm. But Playa is significantly better in terms of the size of the digital nomad community. Plus, of course, it has a beach.
In Playa I met so many different types of workers from so many different countries, doing so many different things. Many of them became close friends who I will make an effort to visit another country just to see.
And that’s when I finally realized something about digital nomad life that I can’t believe hadn’t dawned on me earlier:
There are a lot more ways to make an income online than I had ever thought of.
I had always assumed that most attorney jobs would require me to report to an office.
But it turns out that there was a network of highly respected freelancers who help connect non-traditional but highly qualified lawyers with potential clients.
I decided to take on a couple short term cases to assist another firm with things like writing analyses or doing legal research. But that meant going back to Colorado, since that’s where my license is, while working on those projects.
Anyway, after another quick stint back home, I was able to save some more money and get back on the road – this time with a more stable income stream from my other remote work and a more solid plan of how to attack the task of growing that further.
That’s also when I decided to finally heavily invest in my ventures – both my software company and my travel site.
It paid off: this travel site grew significantly, both in readership and in income.
I was so excited!
I was making a few thousand a month, which is a pittance compared to my previous salary in my corporate attorney job, but enough for my minimalist life on the road.
The Digital Nomad World
This is, after all, one of the fundamental driving forces behind the digital nomad movement that most outsiders do not recognize:
Most digital nomads aren’t living it large in mansions and aren’t blowing their cash on expensive things or even trips.
Digital nomads actually tend to be the modern day versions of Silicon Valley’s fabled garage start-ups, or the creative types who would take a bus to Hollywood and try to get famous while waiting tables to make ends meet, or the starving writers and authors who choose an austere lifestyle because it gives them more inner peace.
And so in some ways it should not come as a surprise that many of the first converts to the school of geo-arbitrage were those types who stand most to benefit from the savings.
But that’s not to say that all digital nomads live any one way.
Digital nomads come from all parts of society and from every sort of background.
I’ve met physical trainers turned digital marketers, college kids who didn’t know what else to do, teachers turned to the freedom of online teaching, and even other lawyers and skilled professionals who just got tired of the corporate grind.
And that lesson was one that also was very important.
Because my original concept of what it mean to be a digital nomad when I set out traveling in 2016 sort of inherently assumed that being a digital nomad had to involve something like “software programming” or “travel blogging.”
In fact, the only digital nomad I had met was my friend Ashwini, a programmer who would essentially dabble in the digital nomad lifestyle by living and working for extended periods in foreign countries but then returning to his home in Denver for longer periods of time.
That of course is the beauty of the travel lifestyle – you can still spend time (often, more meaningful time) at home if you want to.
But alas, Ashwini’s path never seemed liked a practical one for me.
I definitely wasn’t a software engineer.
And the only other thing I could think of that would let you work and travel was travel blogging, so that’s the path I chose.
And since I definitely wasn’t a software programmer, my choice to pursue travel blogging was a simple one.
But I definitely wouldn’t advise most people to go into travel blogging just because they want to travel.
If your goal is just to travel and make money, there are far better ways.
I didn’t realize at the time that there are paths other than that of the creative, technical, and entrepreneurial.
It turns out there are also many professionals who successfully transition to a career at a normal company – simply while working remotely – or manage to convince their existing employer to let them take a period of remote work.
This has even led to a giant industry of large companies that basically act as year-long tour guides for major markups on what you would actually pay to travel to those places yourself.
I don’t personally think they are a great investment, but hey – people are obviously willing to pay a premium for it, so there’s clearly a demand.
What I’ve come to realize over these past three years is that the combination of globalization, the internet, and the rise of the gig economy means that the opportunities to work online while traveling are just going to continue to grow.
Which is great because maybe it means other people won’t have to take such a long and convoluted path as me to the travel lifestyle.
Looking to Transition to a Nomad Life?
How much would I have given to know three years ago what I know today about how to make money online and live the travel lifestyle?
It would have saved me so much time.
And I know from the many messages from my followers who want to know how they can become digital nomads, that many of you today find yourself in the same position I was three years ago: wanting to transition to a travel lifestyle, but not really sure where to begin.
And so I got the idea of helping other people to transition to the travel lifestyle – by providing practical, actionable information that can help save you the trouble I went through to learn it.
If you want some of that info, by the way, just sign up for my digital nomad newsletter in the below email box and I’ll send a copy of “10 Practical Resources for Finding Location Independent Work”:
Concluding Thoughts: It’s Not All Roses – But I Don’t Have Any Regrets
Anyway, I want to mention one more thing before I wrap up:
This whole transition to digital nomad life, which I have slowly learned to embrace, has its drawbacks.
Putting aside the issue of earning a location independent income, there are still plenty of challenges to learning to live a nomadic life.
You have to figure out how to build and maintain relationships, friendships, and a sense of community on the road.
You have to manage your physical and mental well-being without the benefit of the support structures you have back home.
And you have to learn how to sort through the endless administrative annoyances of a nomad life – like taxes, insurance, mail, voting, etc.
It’s not easy and simply finding a remote job is only a small part of the puzzle.
But, for me, the transition to a nomadic lifestyle has brought me happiness and an inner peace that I never had before.
And that I wouldn’t trade for the world.
Because the world is already at my fingertips.